Potassium Carbonate → 5-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

HRID 17525

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](Br)([CH3:15])[CH:4]([C:17]#[N:18])[C:3]=1[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.CB1OB(C)OB(C)O1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([C:17]#[N:18])[C:5]([CH3:15])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8]

Participants

Conditions

Temperature: 110 °C

Procedure

5-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile (I-235) (2.02 g, 6.29 mmol), potassium carbonate (2.61 g, 18.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) were dissolved in 10% water-containing 1,4-dioxane (50 ml), and at room temperature, trimethylboroxine (50 wt. % tetrahydrofuran solution, 1.90 ml, 7.55 mmol) was added. After stirring under nitrogen atmosphere at 110° C. for 8 hours and then cooling to room temperature, tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) was added, followed by further stirring at 110° C. for 11 hours. After cooling to room temperature, the insoluble matter was separated by filtration, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was separated, the aqueous layer was again extracted with ethyl acetate.

Workup

temperaturecooling to room temperature
stirringby further stirring at 110° C. for 11 hours
temperatureAfter cooling to room temperature
customthe insoluble matter was separated by filtration
customThe organic layer was separated
extractionthe aqueous layer was again extracted with ethyl acetate

Sources & evidence

ORD record: ord-41d3ba0b6a6148fcbd9992559d038a83
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

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